Vibratilicin: a Novel Compound from the Basidiomycete Cortinarius vibratilis

Helvetica Chimica Acta
2004.0

Abstract

<jats:title>Abstract</jats:title><jats:p>A novel N‐containing compound, vibratilicin (=3‐[3‐(dimethylamino)‐4‐(hydroxyamino)‐4‐oxobutoxy]‐2‐(palmitoyloxy)propyl (9<jats:italic>E</jats:italic>,12<jats:italic>E</jats:italic>)‐octadeca‐9,12‐dienoate; <jats:bold>1</jats:bold>), was isolated from the fruiting bodies of the basidiomycete <jats:italic>Cortinarius vibratilis</jats:italic> Fr. Compound <jats:bold>1</jats:bold> is a representative of the rare natural products containing hydroxamic acid moieties, and can be viewed as a derivative of neoengleromycin (<jats:bold>2</jats:bold>). Also isolated from the same fungus were five known compounds: ergosta‐5,7,22‐trien‐3<jats:italic>β</jats:italic>‐ol, 5<jats:italic>α</jats:italic>,8<jats:italic>α</jats:italic>‐epidioxyergosta‐6,22‐dien‐3<jats:italic>β</jats:italic>‐ol, <jats:italic>p</jats:italic>‐anisic acid, <jats:italic>N</jats:italic>‐(2‐hydroxyhexadecanoyl)‐4‐sphingenine, and (4<jats:italic>E</jats:italic>,8<jats:italic>E</jats:italic>)‐2‐<jats:italic>N</jats:italic>‐(2′‐hydroxypalmitoyl)‐1‐<jats:italic>O</jats:italic>‐(<jats:italic>β</jats:italic>‐<jats:sc>D</jats:sc>‐glucopyranosyl)‐9‐methyl‐4,8‐sphingadienine. Their structures were determined mainly spectroscopically, including 2D‐NMR techniques (HMBC, HMQC, <jats:sup>1</jats:sup>H,<jats:sup>1</jats:sup>H‐COSY).

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